Brett Chereskin
About

A short bio.

I run operations at a venture-backed fintech and ship AI systems in production.

I’m the COO of dub. My day job is turning a regulated consumer fintech into a company where one operator, leaning on AI, does the work of a team. I build a lot of the tooling myself.

On the side I angel invest in founders doing the same — using AI as leverage, shipping quickly, staying close to customers. I advise a handful of scaling companies on operations and AI adoption.

Before all of that: twelve years in the Army. West Point ’06, Army Aviation. The operator instincts carried over; most of the specifics didn’t.

Career

In reverse chronology.

2022 — PRESENT
COO & Board Member at dub

Partner to the CEO running a venture-backed consumer fintech. I own customer operations, finance, HR and G&A — much of it handled with AI tooling I build in-house.

2018 — 2022
Head of Business Operations at Affirm

Joined as Chief of Staff to the CCO, then built and ran the Business Operations department from scratch through the company’s IPO. Learned how fast-growing fintechs break under regulatory pressure — and what it takes to hold them together when the stakes are real.

2006 — 2018
U.S. Army Officer at Army Aviation

Twelve years in uniform. Fixed-wing reconnaissance, UAS command, and a tour with the 160th Special Operations Aviation Regiment building their first organic large UAS unit from scratch.

Credentials

Licenses & certifications.

  • Commercial PilotFixed Wing & Rotary
    FAA
  • Commercial UAS Certificate
    FAA Part 107
  • Series 99 — Operations Professional
    FINRA
  • Securities Industry Essentials
    FINRA
Where I put my time and money

Advisory and capital.

Angel investor and advisor. I back operators building with AI and help scaling companies adopt it without breaking things.

  • Angel investing

    Early-stage checks into AI-native operators shipping close to their customers. Most recent: Truv, a consumer-permissioned financial data platform.

  • Stage 2 Capital

    Catalyst LP in the B2B go-to-market fund. Active with portfolio companies on operations and scaling.

  • Context Ventures

    Fund LP. Context backs military founders — the leadership and risk calibration translate into a real edge at seed.

  • Advisory

    Advisor to Grady AI (AI-powered grading for higher ed) and a small number of scaling companies on operations, GTM, and AI adoption.

In conversation

Selected appearances.

Off the clock

The other half.

Married to Lisa for thirteen years. We met in Germany while I was flying for the Army and we still go back every chance we get. Our Pomsky, Tanuki, is the best city dog in Manhattan — and the reason we know most of the quiet corners of it.

Long Island kid. After fifteen years of military travel and a stint in San Francisco, I came back to New York and we’ve been making up for lost time — food, wine, and more Broadway than is probably wise.

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